US4061639A - Quinolinesulfonyl compounds - Google Patents
Quinolinesulfonyl compounds Download PDFInfo
- Publication number
- US4061639A US4061639A US05/716,747 US71674776A US4061639A US 4061639 A US4061639 A US 4061639A US 71674776 A US71674776 A US 71674776A US 4061639 A US4061639 A US 4061639A
- Authority
- US
- United States
- Prior art keywords
- quinolinesulfonyl
- hydrazine
- compounds
- bromide
- bromine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- -1 Quinolinesulfonyl compounds Chemical class 0.000 title description 5
- GIKMIPYQLAPSFS-UHFFFAOYSA-N quinoline-8-sulfonyl bromide Chemical compound C1=CN=C2C(S(=O)(=O)Br)=CC=CC2=C1 GIKMIPYQLAPSFS-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 9
- AMZJVFOOYZDELG-UHFFFAOYSA-N quinoline-2-sulfonyl bromide Chemical class C1=CC=CC2=NC(S(=O)(=O)Br)=CC=C21 AMZJVFOOYZDELG-UHFFFAOYSA-N 0.000 abstract description 6
- WCTWEMPLTHNDLQ-UHFFFAOYSA-N quinoline-2-sulfonohydrazide Chemical compound C1=CC=CC2=NC(S(=O)(=O)NN)=CC=C21 WCTWEMPLTHNDLQ-UHFFFAOYSA-N 0.000 abstract description 5
- 239000004599 antimicrobial Substances 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000000845 anti-microbial effect Effects 0.000 description 5
- 150000001649 bromium compounds Chemical class 0.000 description 5
- MNYZCZWQSSEHTN-UHFFFAOYSA-N quinoline-8-sulfonohydrazide Chemical compound C1=CN=C2C(S(=O)(=O)NN)=CC=CC2=C1 MNYZCZWQSSEHTN-UHFFFAOYSA-N 0.000 description 5
- JUYUYCIJACTHMK-UHFFFAOYSA-N quinoline-8-sulfonyl chloride Chemical class C1=CN=C2C(S(=O)(=O)Cl)=CC=CC2=C1 JUYUYCIJACTHMK-UHFFFAOYSA-N 0.000 description 5
- 150000002429 hydrazines Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- VHXJRLYFEJAIAM-UHFFFAOYSA-N quinoline-2-sulfonyl chloride Chemical compound C1=CC=CC2=NC(S(=O)(=O)Cl)=CC=C21 VHXJRLYFEJAIAM-UHFFFAOYSA-N 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000223678 Aureobasidium pullulans Species 0.000 description 2
- 235000014469 Bacillus subtilis Nutrition 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 241000588915 Klebsiella aerogenes Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000187481 Mycobacterium phlei Species 0.000 description 2
- 241000235546 Rhizopus stolonifer Species 0.000 description 2
- 241000235063 Wickerhamomyces anomalus Species 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- YCXYGQKJFPZJOG-UHFFFAOYSA-N quinoline-7-sulfonohydrazide Chemical compound C1=CC=NC2=CC(S(=O)(=O)NN)=CC=C21 YCXYGQKJFPZJOG-UHFFFAOYSA-N 0.000 description 2
- SPXFIWYSRJWBEI-UHFFFAOYSA-N quinoline-7-sulfonyl bromide Chemical compound C1=CC=NC2=CC(S(=O)(=O)Br)=CC=C21 SPXFIWYSRJWBEI-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- GVLMPYSKLDAEBT-UHFFFAOYSA-N quinoline-5-sulfonohydrazide Chemical compound C1=CC=C2C(S(=O)(=O)NN)=CC=CC2=N1 GVLMPYSKLDAEBT-UHFFFAOYSA-N 0.000 description 1
- RUYALBKBGOZQFG-UHFFFAOYSA-N quinoline-5-sulfonyl bromide Chemical compound C1=CC=C2C(S(=O)(=O)Br)=CC=CC2=N1 RUYALBKBGOZQFG-UHFFFAOYSA-N 0.000 description 1
- IGBMUOLGIDEIJH-UHFFFAOYSA-N quinoline-5-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=N1 IGBMUOLGIDEIJH-UHFFFAOYSA-N 0.000 description 1
- ZZGCLAJJDSNUPB-UHFFFAOYSA-N quinoline-6-sulfonohydrazide Chemical compound N1=CC=CC2=CC(S(=O)(=O)NN)=CC=C21 ZZGCLAJJDSNUPB-UHFFFAOYSA-N 0.000 description 1
- ZOBYCOIWGYCYFH-UHFFFAOYSA-N quinoline-6-sulfonyl bromide Chemical compound N1=CC=CC2=CC(S(=O)(=O)Br)=CC=C21 ZOBYCOIWGYCYFH-UHFFFAOYSA-N 0.000 description 1
- AUDKCUOUBLCZQR-UHFFFAOYSA-N quinoline-6-sulfonyl chloride Chemical compound N1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 AUDKCUOUBLCZQR-UHFFFAOYSA-N 0.000 description 1
- ZSLBTAMFISNVKS-UHFFFAOYSA-N quinoline-7-sulfonyl chloride Chemical compound C1=CC=NC2=CC(S(=O)(=O)Cl)=CC=C21 ZSLBTAMFISNVKS-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
Definitions
- the 5-, 6-, 7- and 8-quinolinesulfonyl chlorides are known; for example, see A. A. Albert et al., J. Chem. Soc., 2384 (1959); R. Ponci et al., Farmco (Pavia), Ed. Sci, 9, 459 (1954) and Chem. Abstr., 49, 11657b (1955); A. Claus et al., J. Prakt, Chem., 40, 447 (1889); and G. Buchmann, et al., J. Prakt. Chem., 16, 152 (1962). Their antimicrobial activity is poor.
- novel compounds of this invention are quinolinesulfonyl hydrazine and quinolinesulfonyl bromide compounds of the formula ##STR2## wherein R is either a bromine radical (Br--) or a hydrazine radical (H 2 NHH--).
- novel quinolinesulfonyl hydrazine compounds are herein referred to as "q. hydrazines” and the novel quinolinesulfonyl bromide compounds are herein referred to as "q. bromides”.
- the novel q. hydrazines consist of
- the invention's novel compounds are crystalline solids which are of low solubility in water and of moderate solubility in many organic solvents.
- the q. bromides have been found to have utility in the kill and control of bacterial and fungal organisms.
- the q. hydrazines have utility as intermediates for making the q. bromides.
- the q. hydrazines are prepared by slowly adding substantially one molar proportion of the corresponding quinolinesulfonyl chloride (i.e. either 5-, 6-, 7- or 8-quinolinesulfonyl chloride) to substantially two molar proportions of hydrazine at about 5° C to about 15° C.
- the reaction is advantageously carried out in the presence of an appropriate polar organic solvent, such as, for example, methanol, ethanol or dimethylformamide as reaction medium.
- an appropriate polar organic solvent such as, for example, methanol, ethanol or dimethylformamide
- the q. bromides are prepared by slowly adding substantially four molar proportions of bromine to a solution of substantially one molar proportion of the corresponding q. hydrazine (i.e. either 5-, 6-, 7- or 8-q. hydrazine) in a suitable organic solvent, such as chloroform. Said solution should be cooled, prior to the addition of the bromine, by adding crushed ice thereto. After the addition of the bromine is complete and all of the bromine color has disappeared, the layers of the resulting slurry are separated. The organic layer is dried, such as over anhydrous magnesium sulfate. The solvent is removed, advantageously in vacuo, and the product is recrystallized from the resulting residue from an appropriate organic solvent, advantageously hexane.
- a suitable organic solvent such as chloroform.
- the above process can be utilized to make three isomers of 8-quinolinesulfonyl bromide, namely 5-, 6- and 7-quinolinesulfonyl bromide, by employing the corresponding quinolinesulfonyl hydrazine.
- a 500 ml Erlenmeyer flask equipped with a magnetic stirrer and a thermometer is charged with 200 ml of methanol and 3.40 g (0.10 mol) of 95% hydrazine.
- the solution is cooled to 5° C, and 11.38 g (0.05 mol) of 8-quinolinesulfonyl chloride is added in small portions at a rate such that the reaction temperature does not exceed 15° C.
- the solution is allowed to warm slowly to room temperature.
- the precipitating solid is filtered off to give 8.00 g of 8-quinolinesulfonyl hydrazine (C 9 H 9 N 3 O 2 S), m.p. 135°-137° C.
- the above process can be utilized to make three isomers of 8-quinolinesulfonyl hydrazine, namely 5-, 6- and 7-quinolinesulfonyl hydrazine, by employing the corresponding quinolinesulfonyl chloride.
- the quinolinesulfonyl bromide compounds of the invention are useful as antimicrobial agents for the control of bacteria and fungi. This is not to suggest that these compounds and mixtures thereof with usual additives are equally effective against all such organisms at the same concentration.
- these compounds can be employed in an unmodified form or dispersed on a finely divided solid and employed as a dust. Such mixtures can also be dispersed in water with the aid of a surface-active agent and the resulting emulsion employed as a spray.
- the quinolinesulfonyl bromide compounds can be employed as the active constituents in solvent solutions, oil-in-water or water-in-oil emulsions.
- compositions containing antimicrobial concentrations are adapted to be formulated as concentrates and subsequently diluted with additional liquid or solid adjuvants to produce the ultimate treating compositions. Good results are obtained when employing compositions containing antimicrobial concentrations and usually from about 100 to about 500 parts by weight of one or more of the compounds per million parts of such compositions.
- 8-quinolinesulfonyl bromide is dispersed in warm melted nutrient agar which is then poured into petri dishes and allowed to solidify, the quinoline compound being employed in an amount sufficient to provide from 10 to 500 parts by weight thereof per million parts (ppm) of the ultimate agar composition.
- the surface of the agar is then inoculated with a variety of bacterial and fungal pest organisms, and the inoculated plates are incubated under conditions conducive to bacterial and fungal growth. Similar check plates in which the agar contains no active quinoline or other toxic compound are similarly inoculated and incubated.
- 8-quinolinesulfonyl bromide gave 100% growth inhibition (kills) and control of the following organisms at the indicated concentrations in parts per million:
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Quinolinesulfonyl hydrazine and quinolinesulfonyl bromide compounds of the formula ##STR1## wherein R is either a bromine radical or a hydrazine radical. The quinolinesulfonyl hydrazine compounds are useful as intermediates for making quinolinesulfonyl bromide compounds, the latter being useful as antimicrobials.
Description
The 5-, 6-, 7- and 8-quinolinesulfonyl chlorides are known; for example, see A. A. Albert et al., J. Chem. Soc., 2384 (1959); R. Ponci et al., Farmco (Pavia), Ed. Sci, 9, 459 (1954) and Chem. Abstr., 49, 11657b (1955); A. Claus et al., J. Prakt, Chem., 40, 447 (1889); and G. Buchmann, et al., J. Prakt. Chem., 16, 152 (1962). Their antimicrobial activity is poor.
The novel compounds of this invention are quinolinesulfonyl hydrazine and quinolinesulfonyl bromide compounds of the formula ##STR2## wherein R is either a bromine radical (Br--) or a hydrazine radical (H2 NHH--).
For convenience of description, the novel quinolinesulfonyl hydrazine compounds are herein referred to as "q. hydrazines" and the novel quinolinesulfonyl bromide compounds are herein referred to as "q. bromides".
The novel q. hydrazines consist of
5-quinolinesulfonyl hydrazine;
6-quinolinesulfonyl hydrazine;
7-quinolinesulfonyl hydrazine; and
8-quinolinesulfonyl hydrazine.
The novel q. bromides consist of
5-quinolinesulfonyl bromide;
6-quinolinesulfonyl bromide;
7-quinolinesulfonyl bromide; and
8-quinolinesulfonyl bromide.
The invention's novel compounds are crystalline solids which are of low solubility in water and of moderate solubility in many organic solvents.
The q. bromides have been found to have utility in the kill and control of bacterial and fungal organisms. The q. hydrazines have utility as intermediates for making the q. bromides.
The q. hydrazines are prepared by slowly adding substantially one molar proportion of the corresponding quinolinesulfonyl chloride (i.e. either 5-, 6-, 7- or 8-quinolinesulfonyl chloride) to substantially two molar proportions of hydrazine at about 5° C to about 15° C. The reaction is advantageously carried out in the presence of an appropriate polar organic solvent, such as, for example, methanol, ethanol or dimethylformamide as reaction medium. After the addition of the quinolinesulfonyl chloride is complete, the solution is allowed to slowly warm to room temperature to thereby precipitate the desired product, which is recovered by filtration or other conventional liquids-solids separatory techniques.
The q. bromides are prepared by slowly adding substantially four molar proportions of bromine to a solution of substantially one molar proportion of the corresponding q. hydrazine (i.e. either 5-, 6-, 7- or 8-q. hydrazine) in a suitable organic solvent, such as chloroform. Said solution should be cooled, prior to the addition of the bromine, by adding crushed ice thereto. After the addition of the bromine is complete and all of the bromine color has disappeared, the layers of the resulting slurry are separated. The organic layer is dried, such as over anhydrous magnesium sulfate. The solvent is removed, advantageously in vacuo, and the product is recrystallized from the resulting residue from an appropriate organic solvent, advantageously hexane.
The bromination of arylsulfonyl hydrazines is taught in further detail by Litvinenko et al., Journal of the General Chemistry of the U.S.S.R., Vol. 34, pp. 3780-3782 (1964).
The following examples illustrate the present invention and the manner by which it can be practiced but as such should not be construed as limitations upon the overall scope of the same. The product compounds are identified by elemental analysis and/or nuclear magnetic resonance spectroscopy.
A 500 ml, single-neck flask equipped with a magnetic stirrer is charged with 6.59 g (0.0295 mol) of 8-quinolinesulfonyl hydrazine and 200 ml of chloroform. Crushed ice is added, and the slurry is vigorously stirred. 9.50 g of bromine is added dropwise to the slurry with stirring. After the addition of bromine is complete and all of the bromine color has disappeared, the layers are separated. The chloroform layer is dried over anhydrous magnesium sulfate, and the chloroform is removed in vacuo leaving a pale yellow solid. The solid is slurried with hexane, filtered, and vacuum dried to give 6.00 g (0.221 mol) of 8-quinolinesulfonyl bromide m.p. 142°-144° C.
Anal. -- Calcd. for 8-quinolinesulfonyl bromide (C9 H6 BrNO2 S): C, 39.72; H, 2.22; Br, 29.37; N, 5.14; S, 11.78. Found: C, 39.50; H, 2.30; Br, 28.80 ± 0.2; N, 5.31; S, 12.42.
The above process can be utilized to make three isomers of 8-quinolinesulfonyl bromide, namely 5-, 6- and 7-quinolinesulfonyl bromide, by employing the corresponding quinolinesulfonyl hydrazine.
A 500 ml Erlenmeyer flask equipped with a magnetic stirrer and a thermometer is charged with 200 ml of methanol and 3.40 g (0.10 mol) of 95% hydrazine. The solution is cooled to 5° C, and 11.38 g (0.05 mol) of 8-quinolinesulfonyl chloride is added in small portions at a rate such that the reaction temperature does not exceed 15° C. After the reaction is complete, the solution is allowed to warm slowly to room temperature. The precipitating solid is filtered off to give 8.00 g of 8-quinolinesulfonyl hydrazine (C9 H9 N3 O2 S), m.p. 135°-137° C.
Anal. -- Calcd. for C9 H9 N3 O2 S: C, 48.42; H, 4.06; N, 18.82; S, 14.36. Found: C, 48.40; H, 4.07; N, 18.99; S, 14.30.
The above process can be utilized to make three isomers of 8-quinolinesulfonyl hydrazine, namely 5-, 6- and 7-quinolinesulfonyl hydrazine, by employing the corresponding quinolinesulfonyl chloride.
The quinolinesulfonyl bromide compounds of the invention are useful as antimicrobial agents for the control of bacteria and fungi. This is not to suggest that these compounds and mixtures thereof with usual additives are equally effective against all such organisms at the same concentration. For such uses, these compounds can be employed in an unmodified form or dispersed on a finely divided solid and employed as a dust. Such mixtures can also be dispersed in water with the aid of a surface-active agent and the resulting emulsion employed as a spray. In other procedures, the quinolinesulfonyl bromide compounds can be employed as the active constituents in solvent solutions, oil-in-water or water-in-oil emulsions. The augmented compositions are adapted to be formulated as concentrates and subsequently diluted with additional liquid or solid adjuvants to produce the ultimate treating compositions. Good results are obtained when employing compositions containing antimicrobial concentrations and usually from about 100 to about 500 parts by weight of one or more of the compounds per million parts of such compositions.
In representative activity tests, 8-quinolinesulfonyl bromide is dispersed in warm melted nutrient agar which is then poured into petri dishes and allowed to solidify, the quinoline compound being employed in an amount sufficient to provide from 10 to 500 parts by weight thereof per million parts (ppm) of the ultimate agar composition. The surface of the agar is then inoculated with a variety of bacterial and fungal pest organisms, and the inoculated plates are incubated under conditions conducive to bacterial and fungal growth. Similar check plates in which the agar contains no active quinoline or other toxic compound are similarly inoculated and incubated.
In such operations, 8-quinolinesulfonyl bromide gave 100% growth inhibition (kills) and control of the following organisms at the indicated concentrations in parts per million:
TABLE 1
______________________________________
Antimicrobial Activity of
8-Quinolinesulfonyl Bromide
______________________________________
Organism Conc. in ppm
______________________________________
S. aureus 500
E. coli 100
C. albicans 100
T. mentagrophytes 100
A. niger 100
B. subtilis 100
A. aerogenes 100
C. pelliculosa 100
P. pullulans 100
S. typhosa 100
P. Str-10 100
M. phlei 100
R. nigricans 100
C. ips 100
Trichoderm Sp. Madison P-42
100
______________________________________
In comparative operations, 8-quinolinesulfonyl chloride was tested for antimicrobial activity at 500 ppm using identical agar dilution tests. The following table indicates the percent growth inhibition of the following organisms:
Table 2
______________________________________
Antimicrobial Activity of
8-Quinolinesulfonyl Chloride at 500 PPM
______________________________________
Organism Percent Growth Inhibition
______________________________________
S. aureus 0
E. coli 0
C. albicans 0
P. Str-10 0
S. typhosa 0
M. phlei 50
B. subtilis 0
C. pelliculosa 0
A. aerogenes 0
P. pullulans 0
C. ips 0
Trichoderm Sp. Madison P-42
0
R. nigricans 0
______________________________________
Claims (1)
1. The compound which is 8-quinolinesulfonyl bromide and which corresponds to the formula ##STR3##
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/716,747 US4061639A (en) | 1976-08-23 | 1976-08-23 | Quinolinesulfonyl compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/716,747 US4061639A (en) | 1976-08-23 | 1976-08-23 | Quinolinesulfonyl compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4061639A true US4061639A (en) | 1977-12-06 |
Family
ID=24879270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/716,747 Expired - Lifetime US4061639A (en) | 1976-08-23 | 1976-08-23 | Quinolinesulfonyl compounds |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US4061639A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5047540A (en) * | 1987-12-17 | 1991-09-10 | Shionogi & Co., Ltd. | Lipid derivatives |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2830029A (en) * | 1955-04-28 | 1958-04-08 | American Cyanamid Co | Preparation of cellular products containing organic sulfonyl azides and composition thereof |
| US3714206A (en) * | 1968-12-02 | 1973-01-30 | Gruenenthal Chemie | Benzo-2,3,1-diazaborines |
-
1976
- 1976-08-23 US US05/716,747 patent/US4061639A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2830029A (en) * | 1955-04-28 | 1958-04-08 | American Cyanamid Co | Preparation of cellular products containing organic sulfonyl azides and composition thereof |
| US3714206A (en) * | 1968-12-02 | 1973-01-30 | Gruenenthal Chemie | Benzo-2,3,1-diazaborines |
Non-Patent Citations (7)
| Title |
|---|
| Albert et al., J. Chem. Soc. 2384 (1959). * |
| Buchmann et al., J. Prakt Chem., 16,152, (1962). * |
| Chemical Abstracts, vol. 82, No. 19, 125,260j, (5/12/75). * |
| Chivers, Aust. J. Chem., 1975, 28(2) 413-419, (1975). * |
| Claus et al., J. Prakt Chem. 40, 447, (1889). * |
| McCasland, J. Org. Chem., II, 277-280, (1946). * |
| Ponci et al., Chemical Abstracts, vol. 49, 11,657b, (1955). * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5047540A (en) * | 1987-12-17 | 1991-09-10 | Shionogi & Co., Ltd. | Lipid derivatives |
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